Vacation rentals in Henderson

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Top-rated vacation rentals in Henderson

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite
A welcoming living area features a comfortable sectional sofa adorned with decorative pillows. A sleek coffee table occupies the center, while a modern television is positioned across from the seating. Soft lighting is provided by a ceiling fan, and large windows dressed in dark curtains allow natural light.
Home in Evansville
4.94 out of 5 average rating, 108 reviews

House Near U of Evansville and Ford Center

Stay at this peaceful and centrally located home with fenced yard. The house has been completely remodeled and is located 5 blocks from the University of Evansville and 7 minutes from downtown Evansville for concerts, shows and conventions. The house is located in a quiet safe neighborhood and is 15 minutes from anywhere in town. The house has 2 bedrooms, each with a queen bed, sleeping 4 total. One queen bed has an adjustable base to adjust head and legs in various positions for maximum comfort

Top guest favourite
The exterior of the Hobbit House features unique architectural elements, including curved rooflines and a distinctive round window. A manicured pathway leads to the front door, with greenery surrounding the entrance and decorative outdoor lighting providing subtle illumination.
Home in Evansville
4.97 out of 5 average rating, 104 reviews

Hobbit House 2 bedroom.

Welcome to the Hobbit House! Relax or work from home in this cozy house located in a charming, quiet neighborhood in central Evansville. Each room is curated to set a different vibe from relaxation, sophistication, and fun. This house also has an old speakeasy downstairs filled with arcade games and a movie projector and screen. At night relax in the backyard under a beautifully lit gazebo. This house is also equipped with an office set up to make it easy to work from your home away from home.

Top guest favourite
A contemporary living area features two patterned armchairs beside a small round table with a decorative lamp. Abstract artwork adorns the brick wall, while a textured rug adds comfort underfoot. Soft, ambient light enhances the inviting space.
Loft in Evansville
4.99 out of 5 average rating, 114 reviews

The Cooper I on Franklin (The Ashby Collection)

Right in the heart of Franklin Street! All the “city feels” in this contemporary walk up loft! We provide all the pleasures, perks and pampering of a hotel, but in a fully-furnished private luxury residence. Just steps away from incredible restaurants, bars, pubs, live music, and specialty boutiques. Once you’ve arrived at The Cooper, grab a seat at our window bar overlooking Historic Franklin Street! We have equipped you with everything from a well appointed kitchen to a fabulous hot tub!

Guest favourite
A spacious bed is positioned against a muted green wall, featuring a tufted headboard. Two bedside tables with stylish lamps flank the bed, and a decorative pillow is placed at the center. Soft bedding and a cozy throw add texture to the inviting sleeping area.
Bungalow in Evansville
4.91 out of 5 average rating, 500 reviews

Haven near Haynies on Historic First Street

Warm and cozy with 11ft ceilings and warm wood floors, this 750 sq foot renovated uptown 1 bedroom is just right for your next visit to Evansville. Whether you are in town for work or for play, this is a great spot for you. Located in the same block as Hanies Corner, two blocks from the river trail, and very close to Main Street, Ford Center and Old National events Plaza this home provides a great spot for the active life as well as the night life. Fully equipped, stainless appliances.

Top guest favourite
The exterior of a two-story building is showcased, featuring a red metal roof and a balcony with black chairs. A sign hangs above the entrance, while the river and sunset are visible in the background. A pathway runs alongside the building, with parked cars lining the street.
Loft in Newburgh
4.97 out of 5 average rating, 374 reviews

Riverfront Loft Above Honey Moon Coffee Shop

Located right on the riverfront in downtown Newburgh. Perfect access for walking, hiking, running, or bike riding on the popular riverfront trail. With epic views of the Ohio River including a 2nd story balcony view of beautiful sunrises and sunsets, our stylish loft apartment is located directly over Honey Moon Coffee shop. Please note that the loft is above a coffee shop that opens at 7am each day and you will hear some noise. 2 complimentary drip coffees are included with your stay!

Top guest favourite
Cabin in Dixon
4.96 out of 5 average rating, 326 reviews

Crouse’s North Ninety Lake House

If you want a place where you can be socially distanced, this is the place! (discounts for weekly or monthly stays.) The cabin is set in a 90 acre area surrounded by woods with two small lakes (fishing, walking trails and paddle boating available at no extra charge). There is only one other cabin on the 90 acres. Nearest town, Dixon (3 miles), Madisonville (20 miles, Henderson 21 miles), Evansville, IN (has a regional airport about 35 miles). Truly a relaxing getaway place.

Guest favourite
The entrance to the cabin is framed by wooden siding, featuring a central door adorned with a seasonal wreath. Natural elements, including pumpkins, are arranged on a small porch flanked by rustic decorations and a wooden fence made of branches.
Cabin in Dixon
4.91 out of 5 average rating, 530 reviews

Handcrafted Cabin in Woodsy Heaven

PLEASE read listing before booking. Custom built wood cabin nestled in the rolling hills of western Kentucky. Cozy decor with vintage theme, handcrafted wood floors, and outdoor space overlooking wooded property. Rustic studio space full of modern amenities. Close proximity to 5450 acre Wildlife Management Area with hiking, horseback riding, fishing, hunting, and swimming. Perfect location to get back to nature. Great peaceful weekend or overnight getaway.

Guest favourite
The cabin is showcased with a modern architectural design, featuring a wooden facade and large windows that allow for natural light. The structure sits on a grassy area, with a clear blue sky enhancing the overall appearance.
Cabin in Robards
4.94 out of 5 average rating, 125 reviews

REINE CABIN at Farmer and Frenchman

EAT. TASTE. STAY. Year round view, seasonal flavor. The property features a winery/cafe, a vineyard, walking trails, and a 360 view of countryside. Created in the spirit of rustic elegance, the Cabin's lavish accents are sure to impress. Enjoy dinner in the cafe, walk the trails, snuggle in for the night, order breakfast in bed and a morning yoga session on the patio. Enjoy the ambiance of Kentucky's agrarian heritage with modern and stylish amenities.

Top guest favourite
A historic brick building stands on a cobblestone street, framed by mature trees and shrubs. The entrance features a set of stairs leading to double doors adorned with decorative glass. A lamppost adds charm to the inviting outdoor space.
Apartment in Evansville
4.95 out of 5 average rating, 243 reviews

Victorian 1 Bedroom Guesthouse Apt on 1st Street

This one-bedroom / one-bathroom apartment features high ceilings and exposed brick and is attached to your host’s home - a Victorian townhouse on one of Evansville’s historic cobblestone streets. Enjoy easy self-check-in and a location that is centrally located near the Ohio River, Downtown Evansville, and Haynie’s Corner neighborhoods. The Ford Center, Bally’s Casino, and many of Evansville’s best restaurants and bars are all a short walk away.

Guest favourite
A single-story home with a light blue exterior sits in a quiet neighborhood. The well-maintained front yard features small shrubs and landscaping, while a paved driveway provides easy access. Trees in the background showcase autumn colors, enhancing the peaceful environment.
Home in Evansville
4.87 out of 5 average rating, 102 reviews

Kozy Kathleen

*Currently listed as top 10 AirBnbs in Evansville, IN. *Kozy family home in a quite neighborhood with 2 car capacity drive way including street parking if necessary. *Full of amenities needed for any length of stay. Close to I-69 and HWY 41 for any travel requirements. *Less than 5 miles from the heart beat of Evansville (Ford center/ downtown/ and Eastland mall). *"The Kozy Kathleen" = Real Hoosier home with authentic mid-west feel.

Top guest favourite
Home in Downtown Evansville
4.96 out of 5 average rating, 248 reviews

Rooftop Views in the Heart of Downtown!

Welcome to the Dr. J.R. Mitchell House! Built in 1909 as what is believed to be the first animal clinic in Evansville, this century-old home has been renovated and modernized. Dr. Mitchell's owners' quarters above the original animal clinic now features two bedrooms, an open bunk room for kids, and three full bathrooms. You'll find the original exposed brick throughout the home which adds the perfect vibe to this modern industrial home.

Top guest favourite
Cottage in Owensboro
4.97 out of 5 average rating, 417 reviews

Nature Lovers Retreat

This charming cottage is the perfect getaway for nature lovers. Relax in this home’s cheerful and cozy atmosphere, located on the edge of Ben Hawes Park with over 4 miles of beautiful walking trails and 7.5 miles of bike trails in this gorgeous 297 acre forest. Enjoy all the comforts of home, including free WiFi, TV, washer and dryer, full kitchen, and free parking. This special retreat is also only 1 mile from Ben Hawes Golf Course.

Popular amenities for Henderson vacation rentals

When is the best time to visit Henderson?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Henderson?

    Henderson has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in boutique hotel rentals in Henderson?

    Experience the best of Henderson with our boutique hotel rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Henderson?

    Four-legged friends are welcome in Henderson. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Henderson?

    Yes! Work meets play with ease at over 20 vacation rentals in Henderson featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do boutique hotel rentals in Henderson have air conditioning?

    Absolutely! We offer over 10 boutique hotel rentals with air conditioning in Henderson. Enjoy a tailored experience with all the comforts you desire.

  • Do boutique hotel rentals in Henderson have wifi?

    Absolutely! We offer over 10 boutique hotel rentals with wifi in Henderson. Enjoy a tailored experience with all the comforts you desire.

  • Do boutique hotel rentals in Henderson have free parking?

    Absolutely! We offer over 10 boutique hotel rentals with free parking in Henderson. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Boutique Hotel Rentals in Henderson?

    Enhance your stay in our Boutique Hotel Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Henderson

  • Total vacation rentals

    Explore 30 vacation rentals in Henderson

  • Nightly prices starting at

    Henderson vacation rentals start at $41 CAD per night before taxes and fees

  • Verified guest reviews

    Over 470 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Henderson vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Henderson rentals

  • 4.6 Average rating

    Henderson stays receive an average rating of 4.6 out of 5 from guests

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